Oils used in metalworking typically contain mono- and diethanolamine based fatty acid amides, which are suspected carcinogens, and/or petroleum based hydrocarbons, which can damage the environment. Plant oils are an environmentally friendly alternative to such products, and are based on renewable natural resources. The major components of plant oils are triacylglycerols (TAGs), which contain three fatty acid chains esterified to a glycerol moiety. The polar glycerol regions and non-polar hydrocarbon regions of TAGs are thought to align at the boundaries of metal surfaces and provide boundary lubrication, and thus have better lubricant properties than petroleum hydrocarbons. The negligible water-solubility of plants oils, however, limits their use for water-based applications such as metalworking.